Diguanidino and "reversed" diamidino 2,5-diarylfurans as antimicrobial agents

Journal of Medicinal Chemistry

Volumn 44, Issue 11, 2001, Pages 1741-1748

  Stephens, C E ^a   Tanious, F ^a   Kim, S ^a,b   Wilson, W D ^a   Schell, W A ^c   Perfect, J R ^c   Franzblau, S G ^d   Boykin, D W ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

^b FURMAN UNIVERSITY   (United States)

^c DUKE UNIVERSITY MEDICAL CENTER   (United States)

^d UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 BIS(4 GUANIDINO 2 METHYLPHENYL)FURAN; 2,5 BIS[2 METHOXY 4 (2 PYRIDYLIMINO)AMINOPHENYL]FURAN; 2,5 BIS[2 METHYL 4 (2 PYRIDYLIMINO)AMINOPHENYL]FURAN; 2,5 BIS[2 METHYL 4 (5 METHYL 2 PYRIDYLIMINO)AMINOPHENYL]FURAN; 2,5 BIS[4 (BENZIMIDOYLAMINO)PHENYL]FURAN; 2,5 BIS[4 (PYRIDYLIMINO)AMINOPHENYL]FURAN; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; FLUCONAZOLE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BINDING AFFINITY; CANDIDA ALBICANS; CRYPTOCOCCUS NEOFORMANS; DNA BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; MELTING POINT; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; RHIZOPUS; STRUCTURE ANALYSIS; THERMAL ANALYSIS;

AMIDINES; AMINOPYRIDINES; ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; DNA; FURANS; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035942517     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000413a     Document Type: Article

References (49)

1. Studies in chemotherapy. XIX. Further report on new trypanocidal substances
2. Inhibition of Cryptosporidium parvum in neonatal Hsd: (ICR)BR Swiss mice by polyether ionophores and aromatic amidines
3. Structure-activity relationships of nitidine analogues against Giardia lamblia and correlation of antigiardial activity with DNA-binding affinity
4. Structure-activity relationships of analogues of pentamidine against plasmodium falciparum and leishmania mexicana amazonensis
5. The use of certain aromatic diamidines in the treatment of kala-azar
6. The course of plasmodium relictum infection in canaries and the treatment of bird and monkey malaria with synthetic bases
7. Ein neues behandlungsverfahren der interstitiellen plasmazelligen pneumonierühgeborener mit fünfwertigem stibium und aromatischen diamidinen
8. Dicationic diarylfurans as anti-pneumocystis carinii agents
9. 2,5-bis[4-(N-alkylamidino)phenyl]furans as anti-pneumocystis carinii agents
10. 2,4-Diphenyl furan diamidines as novel anti-pneumocystis carinii pneumonia agents
11. Activity of pentamidine and pentamidine analogues against T. gondii in cell cultures
12. Studies in chemotherapy. XXI. The trypanocidal action of certain aromaticdiamidines
13. Studies in chemotherapy. XXII. The action of certain aromatic diamidines on Babesia canis infections of puppies
14. Synthesis and antiprotozoal activity of 2,5-bis(4-guanylphenyl)furans
15. In vitro activity of dicationic aromatic compounds and fluconazole against Cryptococcus neoformans and Candida species
16. Structure-in vitro activity relationships of pentamidine analogues and dicationic-substituted bis-benzimidazoles as new antifungal agents
17. In vitro antifungal activities of a series of dicationsubstituted carbazoles, furans, benzimidazoles
18. Present status of chemotherapy and chemoprophylaxis of human trypanosomiasis in the eastern hemisphere
19. Visceral leishmaniasis unresponsive to antimonial drugs. II. Response to high dosage sodium stibogluconate or prolonged treatment with pentamidine
20. Efficacy of trimethoprim and sulfamethoxazole in the prevention and treatment of pneumocystis carinii pneumonia
21. Different binding mode in AT and GC sequences for unfused-aromatic dications
22. Nucleic acid interactions of unfused aromatic cations: Evaluation of proposed minor-groove, major-groove and intercalation binding modes
23. Relationships between topoisomerase II inhibition, sequence-specificity and DNA binding mode of dicationic diphenylfuran derivatives
24. Large hydrophobic contributions are involved in DNA minor-groove complex formation with a series of diphenylfuran dications: Surface plasmon resonance isothermal titration calorimetry studies
25. 2
26. Visualization of extensive water ribbons and network in a DNA minor-groove drug complex
27. A crystallographic and spectroscopic study of the complex between d(CGCGAATTCGCG)2 and 2,5-bis(4-guanylphenyl)furan, an analogue of berenil. Structural origins of enhanced DNA-binding affinity
28. Effects of analogues of the DNA minor groove binder hoechst 33258 on topoisomerase I and II mediated activity
29. Structure-activitystudies of dicationic substituted bis-benzimidazoles against giardia lamblia: Correlation of antigiardial activity with DNA binding affinity and giardial topoisomerase II inhibition
30. Selective inhibition of topoisomerases from pneumocystis carinii compared with that of topoisomerases from mammalian cells
31. Identification and characterization of an endo/exonuclease in Pneumocystis carinii that is inhibited by dicationic diarylfurans with efficacy against pneumocystis pneumonia. Implications for mechanism of antimicrobial action
32. Molecular struggle for transcription control
33. Selective nucleosome disruption by drugs that bind in the minor groove of DNA
34. Dicationic furans inhibit development of Cryptosporidium parvum in HSD/ICR suckling mice
35. Studies in chemotherapy. XVI. The trypanocidal action of synthalin
36. Palladium catalyzed cross-coupling reactions for the synthesis of 2,5-disubstituted-furans
37. Synthesis of 2,5-bis(4-cyanophenyl)furan
38. A convenient synthesis of di(benzyloxycarbonyl)-protected guanidines
39. S-2-naphthylmethyl thioacetimidate hydrobromide: A new odorless reagent for the mild synthesis of substituted acetamidines
40. N-phenylamidines as selective inhibitors of human neuronal nitric oxide synthase: Structure activity studies and demonstration of in vivo activity
41. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium
42. Susceptibility testing and bioassay procedure
43. Steric effects on mesomerism. XIII. Preparation of 2,6-dimethyl-4-nitroaniline
44. The fluorine-19 NMR spectra of some fluoroaryl mercurials and the electronic effect of mercury substituents
45. Models for intramolecular exchange in organic π-conjugated open-shell systems: 3-nitrophenyl units connected by 2,5-furandiyl, 2,5-thiophenediyl,and 2,5-pyrrolediyl nonalternant exchange linkers
46. A new synthesis of aliphatic and aromatic thioamides from nitriles
47. Compounds containing thiazole, phenyl, and pyridine rings in chain linkages
48. The synthesis and stereochemistry of quinolizidines and the monomethylquinolizidines, and of their salts and quaternary salts